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My application works in the following way:
The browsers are configured with a local proxy which is an instance of Stunnel running in Client mode that connects to a remote server to another instance of Stunnel running in Server mode that directs the traffic through a real proxy.

I understand there's a bug in IE that requires a workaround in Stunnel - adding TIMEOUTclose = 0 in the configuration.

My question is where should I put this directive ? In the Stunnel Client configuration or in Stunnel Server configuration ?

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So your setup looks something like this:

IE <--plaintext--> (stunnel client) <--TLS--> (stunnel server) <--plaintext--> proxy

The bug you're referring to applies to IE's TLS/SSL implementation, but in your setup IE isn't communicating with TLS. Therefore you don't need it.

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the setup also allows for IE to perform HTTPS requests through Stunnel. In such a case IE will use TLS, won't it ? – Guy Aug 15 '12 at 8:37

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